Startup Fundraising Lessons For The 99%

[This is a weekly series that brings you raw, first-hand experiences from founders and investors in the trenches. Their story submissions are anonymous, allowing them to share openly without fear of retribution. Every Wednesday, we'll run one new story chosen by Dana Severson, who operates StartupsAnonymous, a place for startups to share, ask questions, and answer them in story-length posts, all anonymously.]

I've just recently wrapped up my second funding round and it wasn't any easier than the first. Every aspect, from the deck to the term sheet sucked. I gave up on numerous occasions, only to be shown a ray of light that kept me going.

At the end of this grueling five month process, I end up stumbling across this drivel: Was Y Combinator worth it.

While it's an interesting comparison on the value of YC, one thing stuck with me: This doesn't provide any value for the 99 percent of us that don't have the YC stamp of approval.

One glaring difference is inbound intros. Mr. YC alum stated that all 43 that invested (which, by the way, is a terribly large number of investors) were a result of inbound intros. Nobody they considered an outbound intro converted into an investor.

In fact, he went so far to say that requesting an outbound intro was "a significant waste of time." He further stated that by requesting an intro from a friend, you were essentially jeopardizing your relationship with said friend, and the relationship your friend had with the investor.

While I applaud his audacity, the fact remains that inbound intros are a luxury reserved for those with a lot of hype.

For the 99 percent of us that don't have the low hanging fruit to pick from and are forced to **jeopardize** our friendships in order to raise, here are some potentially useful lessons, in no particular order, from my experience:

Make a wish list of at least 100 investors that make sense for your business. A real list, not just a list of the 100 biggest names. Then, start connecting the dots.

Make the intro request super easy for your friend. Keep it short and easy to forward without editing. Then, and this is important, follow up with your friend to tell them how it turned out. Don't make them wonder.

Self-syndicate from day one. Avoid getting into a "search for a lead." If one comes to you, great, but don’t go looking for it.

Look at whoever is being featured on AngelList and mimic their profile. Don’t copy it, just do as much as they’ve done. AngelList cares immensely about complete and sexy profiles.

Schedule meetings on the same day, even if you're doing them in person. Create artificial urgency by compressing your meetings.

If you get a commitment early in your fundraising process, send them a confirmation request on AngelList. This commits them publicly amongst their peers.

A good and cheap branding tactic: Host your deck on a site you own and get the investor to visit the site to view the deck. Create a retargeting campaign driven by this page.

Another cheap idea: Create a keyword campaign for the top investors on your list. Use their names as the keywords. They sure as hell Google themselves, and when they do, there you are.

If you have an in-person meeting scheduled with an investor and they're unreasonably late (with no warning), leave. Get up and walk out and don't contact them again. This is a level of disrespect that you shouldn't be willing to tolerate. If they're truly sorry, they'll contact you. This happened to us twice. Both times we walked out. One ended up investing.

When meeting with an investor and they're blatently disrespectful, end the meeting early, on your terms. There is so much arrogance, it's sickening.

During the first meeting, if they're not giving you signs (verbal or non-verbal) of interest, there is a 99.9 percent chance they will never invest. I have no donut charts to present this as fact, just my experience.

When you get a rejection email, don't waste your time trying to convince them they're wrong. It won't work. The desperation in that approach is worse than simply moving on. But do take their feedback seriously. See if it's something you can address in your presentation in the future, especially if it's a consistent reason for rejection.

We had an Angel investor that couldn't make a decision after seven calls. If an angel investor can't give you a decision after three calls, move on. We learned this lesson the hard way.

Just because you requested the intro and asked for the meeting, it doesn't mean that you have to do all of the convincing. Always remember, you're looking for a partner, not just money. The meeting is always a two-way evaluation.

Always say that you're raising less than you actually want. If you want to raise $1 million, tell investors you're raising $750,000. This tactic will come in handy when they ask you how much has already been committed. Always answer in percentages, not actual numbers.

Be aware of an investors complete portfolio, not just what they show on AngelList. We had a first-call with an angel fund (that was inbound), who used our call as competitive intelligence gathering. Had we taken a closer look at their portfolio before the call, we would have known they had already invested in our chief competitor.

All associates aren't bad, but generally speaking, they're a waste of your time.

Figure out a way to spot the posers. I'm not sure if I'll ever understand why people pretend to be investors, but they do. Between two posers, we wasted over four hours.

The invest online option through AngelList didn't work for us. AL doesn't do a good job promoting the companies using this feature. It's not their fault it didn't work, but if you want to raise online, there are other platforms that do a better job promoting their companies.